JP4520712B2 - フルオロハロゲンエーテル類の製造法 - Google Patents
フルオロハロゲンエーテル類の製造法 Download PDFInfo
- Publication number
- JP4520712B2 JP4520712B2 JP2003286161A JP2003286161A JP4520712B2 JP 4520712 B2 JP4520712 B2 JP 4520712B2 JP 2003286161 A JP2003286161 A JP 2003286161A JP 2003286161 A JP2003286161 A JP 2003286161A JP 4520712 B2 JP4520712 B2 JP 4520712B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- cof
- iii
- fluorine
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 34
- 150000002170 ethers Chemical class 0.000 title claims description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 87
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 41
- 239000011737 fluorine Substances 0.000 claims abstract description 41
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 239000007791 liquid phase Substances 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000000460 chlorine Substances 0.000 claims description 33
- 150000001336 alkenes Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 16
- 150000001265 acyl fluorides Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 238000010924 continuous production Methods 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- -1 fluoro halogens ethers Chemical class 0.000 claims description 5
- UPVJEODAZWTJKZ-OWOJBTEDSA-N (e)-1,2-dichloro-1,2-difluoroethene Chemical group F\C(Cl)=C(\F)Cl UPVJEODAZWTJKZ-OWOJBTEDSA-N 0.000 claims description 3
- HATFLOWGZBUEIE-UHFFFAOYSA-N 1,2-dibromo-1,2-difluoroethene Chemical group FC(Br)=C(F)Br HATFLOWGZBUEIE-UHFFFAOYSA-N 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 34
- VMUWIFNDNXXSQA-UHFFFAOYSA-N hypofluorite Chemical compound F[O-] VMUWIFNDNXXSQA-UHFFFAOYSA-N 0.000 description 31
- 239000003054 catalyst Substances 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000004817 gas chromatography Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000003682 fluorination reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000006471 dimerization reaction Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- YLCLKCNTDGWDMD-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)F YLCLKCNTDGWDMD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- AOMUALOCHQKUCD-UHFFFAOYSA-N dodecyl 4-chloro-3-[[3-(4-methoxyphenyl)-3-oxopropanoyl]amino]benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=C(Cl)C(NC(=O)CC(=O)C=2C=CC(OC)=CC=2)=C1 AOMUALOCHQKUCD-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GVGCUCJTUSOZKP-UHFFFAOYSA-N nitrogen trifluoride Chemical class FN(F)F GVGCUCJTUSOZKP-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- WMFABESKCHGSRC-UHFFFAOYSA-N propanoyl fluoride Chemical compound CCC(F)=O WMFABESKCHGSRC-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT001782A ITMI20021782A1 (it) | 2002-08-06 | 2002-08-06 | Processo per preparare fluoroalogenoeteri. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004067693A JP2004067693A (ja) | 2004-03-04 |
| JP4520712B2 true JP4520712B2 (ja) | 2010-08-11 |
Family
ID=30130963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003286161A Expired - Lifetime JP4520712B2 (ja) | 2002-08-06 | 2003-08-04 | フルオロハロゲンエーテル類の製造法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6835856B2 (de) |
| EP (1) | EP1388531B1 (de) |
| JP (1) | JP4520712B2 (de) |
| CN (1) | CN1280247C (de) |
| DE (1) | DE60323793D1 (de) |
| IT (1) | ITMI20021782A1 (de) |
| RU (1) | RU2329247C2 (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20030150A1 (it) * | 2003-01-30 | 2004-07-31 | Solvay Solexis Spa | Processo per preparare fluoroalogenoeteri. |
| ITMI20030444A1 (it) * | 2003-03-11 | 2004-09-12 | Solvay Solexis Spa | Processo per preparare (per)fluoroalogenoeteri. |
| ITMI20040132A1 (it) | 2004-01-29 | 2004-04-29 | Solvay Solexis Spa | Processo per preparare fluoroalogenoeteri |
| ITMI20040133A1 (it) | 2004-01-29 | 2004-04-29 | Solvay Solexis Spa | Processo per preparare fluoroalogenoeteri |
| ITMI20041253A1 (it) * | 2004-06-22 | 2004-09-22 | Solvay Solexis Spa | Gel di fluoroelastomeri |
| ITMI20050817A1 (it) | 2005-05-05 | 2006-11-06 | Solvay Solexis Spa | Processo di dealogenazione |
| RU2497801C1 (ru) * | 2012-07-18 | 2013-11-10 | Закрытое акционерное общество научно-производственное Объединение "ПиМ-Инвест" (ЗАО НПО "Пим-Инвест") | Окса- и полиоксаперфторалкилбромиды и способ их получения |
| WO2015014735A1 (en) | 2013-08-01 | 2015-02-05 | Solvay Specialty Polymers Italy S.P.A. | Fluorinated compounds containing a -osf5 group and process for their preparation |
| WO2016089617A1 (en) * | 2014-12-01 | 2016-06-09 | 3M Innovative Properties Company | Methods of making halogenated fluorinated ether-containing compounds |
| CN105254476A (zh) * | 2015-11-05 | 2016-01-20 | 中蓝晨光化工研究设计院有限公司 | 一种制备含氟卤代醚的方法 |
| WO2020187839A1 (en) * | 2019-03-18 | 2020-09-24 | Solvay Specialty Polymers Italy S.P.A. | Heat exchange method using fluorinated compounds having a low gwp |
| CN115703698A (zh) * | 2021-08-12 | 2023-02-17 | 中国科学院上海有机化学研究所 | 三氟乙烯基烷基醚类化合物及其中间体的制备方法 |
| CN114656338A (zh) * | 2022-04-24 | 2022-06-24 | 四川道宏新材料有限公司 | 一种全氟正丙基乙烯基醚的合成方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS625932A (ja) * | 1985-05-17 | 1987-01-12 | アウシモント・ソチエタ・ペル・アツイオニ | フルオルハロエ−テル及びそれらの製造法 |
| JPS63198641A (ja) * | 1986-11-14 | 1988-08-17 | アウシモント・ソチエタ・ペル・アツィオニ | フルオルオキシ化合物とハロゲン化オレフィンを出発物質とするフルオルハロゲン化エーテルの製造方法 |
| JPH02169532A (ja) * | 1988-12-22 | 1990-06-29 | Tokuyama Soda Co Ltd | 含フッ素エーテル化合物の製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3453333A (en) * | 1965-10-01 | 1969-07-01 | Allied Chem | Fluorinated ethers |
| JPS5630935A (en) * | 1979-08-22 | 1981-03-28 | Asahi Glass Co Ltd | Preparation of compound having omega-hydro- perfluoroalkaneoxymethyl group |
| IT1184149B (it) * | 1985-03-11 | 1987-10-22 | Montefluos Spa | Processo per la preparazione di fluorossi-alo-composti |
| IT1197474B (it) * | 1986-09-08 | 1988-11-30 | Ausimont Spa | Bromofluroetilipofluorito e procedimento per la sua preparazione |
| IT1197476B (it) * | 1986-09-10 | 1988-11-30 | Ausimont Spa | Ipofluoriti e bis-ipofluoriti e procedimento per la loro preparazione |
| IT1230718B (it) * | 1989-02-13 | 1991-10-29 | Ausimont Srl | Fluorurazione diretta di fluoro b sultoni ai corrispondenti fluorossi fluorosulfonil fluorocomposti. |
| IT1269517B (it) * | 1994-05-19 | 1997-04-01 | Ausimont Spa | Polimeri e copolimeri fluorurati contenenti strutture cicliche |
-
2002
- 2002-08-06 IT IT001782A patent/ITMI20021782A1/it unknown
-
2003
- 2003-07-29 EP EP03017180A patent/EP1388531B1/de not_active Expired - Lifetime
- 2003-07-29 DE DE60323793T patent/DE60323793D1/de not_active Expired - Lifetime
- 2003-08-04 JP JP2003286161A patent/JP4520712B2/ja not_active Expired - Lifetime
- 2003-08-05 RU RU2003124017/04A patent/RU2329247C2/ru not_active IP Right Cessation
- 2003-08-05 US US10/633,565 patent/US6835856B2/en not_active Expired - Lifetime
- 2003-08-06 CN CNB031580378A patent/CN1280247C/zh not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS625932A (ja) * | 1985-05-17 | 1987-01-12 | アウシモント・ソチエタ・ペル・アツイオニ | フルオルハロエ−テル及びそれらの製造法 |
| JPS63198641A (ja) * | 1986-11-14 | 1988-08-17 | アウシモント・ソチエタ・ペル・アツィオニ | フルオルオキシ化合物とハロゲン化オレフィンを出発物質とするフルオルハロゲン化エーテルの製造方法 |
| JPH02169532A (ja) * | 1988-12-22 | 1990-06-29 | Tokuyama Soda Co Ltd | 含フッ素エーテル化合物の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2003124017A (ru) | 2005-03-10 |
| EP1388531B1 (de) | 2008-10-01 |
| DE60323793D1 (de) | 2008-11-13 |
| RU2329247C2 (ru) | 2008-07-20 |
| CN1280247C (zh) | 2006-10-18 |
| ITMI20021782A1 (it) | 2004-02-07 |
| US6835856B2 (en) | 2004-12-28 |
| JP2004067693A (ja) | 2004-03-04 |
| US20040030146A1 (en) | 2004-02-12 |
| EP1388531A1 (de) | 2004-02-11 |
| CN1488616A (zh) | 2004-04-14 |
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